How much should you primp for a date? It’s all relative

Last weekend, I had the terrible opportunity to see myself objectively: I was organizing boxes of old photos, finding iterations of myself at 16, 17, and 18, and realized that I look almost exactly the same.

My hair, then as now, still defaults to a messy bun. My party clothes have been upgraded maybe 6,000 per cent, but my daywear still recalls the sartorial lineage of Bart Simpson.

Men, millennial or not, aren’t as super-socialized as women to work on or even really consider their look, writes Kate Carraway.

The marginal effort that I continue to make with outfits and grooming is contiguous with the millennial habit of misunderstanding the concept of effort as what we make for ourselves, not for other people. The idea of dressing and grooming “appropriately” to demonstrate respect and reverence for the people around us, and for particular social occasions, just kind of missed us, in part because culture has been aggressively de-etiquetteing for more than half a century, in part because we are a super-individuated, self-interested generation, and in part because, currently, sports bras are shirts, crop tops are business formal, and bandanas are costume jewelry.

This has an obvious effect on work and office culture, and even more on dating. Meeting someone online takes less effort than making a smoothie; lack of effort is the very foundation of dates that start with cellphone photos, oblique microautobiographies, declarative swipes and inert opening lines, a barely adult version of the “Yes” and “No” boxes on notes passed between crushed-out adolescents. The lack of attention paid to clothes and shoes — the shoes! — and hair and skin and nails seems inevitable in contemporary dating, where discomfort and vulnerability is part of the deal even if the date itself was made via thumb-text, and is reason enough to wear the same whatever-stuff that’s acceptable, even appropriate, everywhere else you go.

I get a lot of email from readers — for the Dating Diaries, and otherwise — about their romantic lives; predictably, it’s a lot about dates wearing the wrong clothes: dirty clothes, old clothes, ill-fitting clothes, wrinkled clothes. There’s also dirty hair, bad breath, wild eyebrows, malodour. Women complain more about the way that men present themselves on dates (and how men behave: first, not asking any questions, and second, going in for a kiss after an objectively bad date), but men complain more about women. Older, non-millennial women dating after divorce are, it seems, the most unimpressed with what their dates wear, those fashion decisions made, maybe, without the oversight of a wife for the first time in a while.

Men, millennial or not, aren’t as super-socialized as women to work on or even really consider their look. When I ask them how they prepared for their date, they don’t know what I mean. Or when I ask what they wore, they forgot.

Grooming matters because it’s part of attraction, and attraction is the most subjective part of a subjective process. Other elements of dating are more democratized: correcting for bigoted daters, who discriminate for reasons more significant than the tuck of a shirt, the promise of dating sites and apps is that they’re less firmly tied to the social and class-based contexts that come from meeting someone at work or school or through friends. With online dating, it's much more likely that your date will be very different than you, which can be great, and which can also create problems when it comes to what is and isn't appropriate to wear, say or do on a date.

Kate Carraway is a Toronto-based writer and a freelance contributing columnist for the Star. Follow her on Twitter: @KateCarraway